This invention relates to novel sulfonylurea compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within this class of herbicides, but they generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--,
U.S. No. 4,369,320 and U.S. No. 4,453,970 disclose herbicidal quinolinylsulfonylureas.
U.S. No. 4,391,627 discloses herbicidal benzothiophenesulfonylureas.
EP-A-70,698 published 1/26/83 discloses herbicidal indolesulfonylureas.
EP-A-146,263, published 6/26/85 discloses herbicidal sulfonylureas of the formula ##STR1## wherein J is ##STR2## E is a bridge of 3 or 4 atoms, which may be substituted or unsubstituted, containing 0 to 2 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and also containing 1-4 atoms of carbon, said bridge together with two carbon attachment sites forming a partially saturated 5- to 6-membered carbocyclic or heterocyclic ring; or E is a bridge of 3 or 4 atoms which may be substituted or unsubstituted containing at least 1 heteroatom selected from 0-1 oxygen or sulfur or 0-2 nitrogen and 1-3 atoms of carbon, said bridge together with two carbon attachment sites forming an unsaturated 5- to 6-membered heterocyclic ring, with the proviso that when E contains two atoms of oxygen or sulfur, then they must be separated by at least one atom of carbon and that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO.sub.2 ; in the bridging group E, nitrogen may take the form of N or N--O, sulfur may take the form of S, SO or SO.sub.2, and one of the atoms of carbon may be a carbonyl, thiocarbonyl or the cyclic 5- and 6-membered ketals thereof; and
G is O, S, NH or NCH.sub.3. PA1 J, in part, is CH.sub.2, C(O), S(O).sub.m, O, NH or NCH.sub.3 ; PA1 n and n.sub.1 are independently 0 or 1; and PA1 E is a bridge of 3 or 4 atoms containing 0-2 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, wherein 1 atom of sulfur may take the form of SO or SO.sub.2, said bridge also containing 1 to 4 atoms of carbon wherein 1 atom of carbon may take the form of C.dbd.O, said bridge together with two attachment sites forming a non-aromatic heterocyclic or carbocyclic ring optionally substituted by 1 to 3 substituent groups selected from the group L, or E is a bridge of 3 or 4 atoms containing 0-1 heteroatoms of oxygen or sulfur and 0-3 heteroatoms of nitrogen, said bridge also containing 0-4 atoms of carbon, said bridge together with two attachment sites forming an aromatic heterocyclic or carbocyclic ring optionally substituted by 1 to 3 substituents selected from the group L, with the proviso that when E contains two oxygen atoms or two sulfur atoms said atoms must be separated by at least one atom of carbon and that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO.sub.2 ; PA1 A, in part is ##STR18## Z is CH, N, CCH.sub.3, CEt, CCl or CBr; Z.sub.1 is C--U, N or N--O; PA1 Z.sub.2 and Z.sub.3 are independently N or C--U; PA1 Z.sub.4 is NCH.sub.3, O, S or CH.sub.2 ; and PA1 U is H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl optionally substituted by F, Cl, Br or OCH.sub.3, CN, NO.sub.2, NMe.sub.2, OR.sub.22, or SR.sub.22, or CO.sub.2 CH.sub.3. PA1 W is O or S; PA1 R.sub.1 and R.sub.2 are independently alkyl, alkoxy or halogen; and PA1 Z is CH or N. PA1 R.sup.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 haloalkoxy or C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3, SCH.sub.3 or CN; PA1 R.sup.3 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sup.4 is H or CH.sub.3 ; PA1 R.sup.5 is H, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, OR.sup.6, SR.sup.6, S(O).sub.2 R.sup.6, CO.sub.2 R.sup.7, C(O)NR.sup.8 R.sup.9, S(O).sub.2 NR.sup.10 R.sup.11, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 haloalkenyl, C.sub.2 -C.sub.3 alkynyl, NO.sub.2, CN, C(O)R.sup.12, or C.sub.1 -C.sub.2 alkyl substituted by C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or CN; PA1 R.sup.6 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.3 alkenyl, C.sub.2 -C.sub.3 haloalkenyl, propargyl, cyclopropyl, cyclopropylmethyl or --CH.sub.2 CH.sub.2 -- substituted by OH, C.sub.1 -C.sub.2 alkoxy, SH, C.sub.1 -C.sub.2 thioalkyl or CN; PA1 R.sup.7 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 haloalkyl, allyl, propargyl, cyclopropyl, cyclopropylmethyl, or --CH.sub.2 CH.sub.2 -- substituted by OH, OCH.sub.3, SCH.sub.3 or CN; PA1 R.sup.8 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sup.9 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, allyl, propargyl, cyclopropyl, CH.sub.2 CN, CH.sub.2 CH.sub.2 CN Or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sup.10 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sup.11 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, allyl, propargyl, cyclopropyl, cyclopropylmethyl, CH.sub.2 CN, CH.sub.2 CN, CH.sub.2 CH.sub.2 CN or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sup.10 and R.sup.11 can be taken together to form a ring consisting of (--CH.sub.2 --).sub.4, (--CH.sub.2 --).sub.5 or (--CH.sub.2 CH.sub.2 --).sub.2 O; PA1 R.sup.12 is H, C.sub.1 -C.sub.3 alkyl or cyclopropyl; PA1 R.sup.13 is H, C.sub.1 -C.sub.3 alkyl, cyclopropyl, Cl, CN, OCH.sub.3, SCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sup.14 is H or C.sub.1 -C.sub.3 alkyl; PA1 Z is N or CH; PA1 Z.sup.1 is N, CH or CCH.sub.3 ; PA1 Z.sup.2 is O, S or NCH.sub.3 ; PA1 Z.sup.3 is O, S or N--R.sup.15 ; PA1 R.sup.15 is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 SCH.sub.3, CH.sub.2 CN or CO.sub.2 CH.sub.3 ; PA1 W is O or S; PA1 R is H or CH.sub.3 ; PA1 A is ##STR22## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkyl thioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR23## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 Q.sub.1 and Q.sub.2 are independently O or S; PA1 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA1 Z.sup.4 is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Z.sup.5 is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (l) when X is halogen, then Z.sup.4 is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCF.sub.2 H, OCF.sub.2 Br or N(OCH.sub.3)CH.sub.3 ; PA1 (2) when X or Y is C.sub.1 haloalkoxy, then Z.sup.4 is CH; PA1 (3) when W is S, then R is H, A is A-1, Z.sup.4 is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR24## (4) when the total number of carbon atoms of X and Y is greater than four, then the greatest combined number of carbons of any two substituents on an L, selected from R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.15 is less than or equal to six; PA1 (5) X.sub.4 and Y.sub.4 are not simultaneously Cl; PA1 (6) the total number of carbon atoms of R.sup.10 and R.sup.11 is less than or equal to five. PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR25## OCF.sub.2 H, OCF.sub.2 Br, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ; PA1 R.sub.a is H or CH.sub.3 ; and PA1 R.sub.b and R.sub.c are independently CH.sub.3 or CH.sub.2 CH.sub.3. PA1 R.sup.1 is H, halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, OR.sup.6, SR.sup.6, S(O)R.sup.6, S(O).sub.2 R.sup.6, CO.sub.2 R.sup.7, C(O)NR.sup.8 R.sup.9, S(O).sub.2 NR.sup.10 R.sup.11, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 haloalkenyl, NO.sub.2, CN, C(O)R.sup.12, C(R.sup.13).dbd.NOR.sup.14 or C.sub.1 -C.sub.2 alkyl substituted by C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or CN; PA1 R.sup.2 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sup.5 is H, halogen, C.sub.1 -C.sub.2 alkyl, PA1 C.sub.1 -C.sub.2 haloalkyl, OR.sup.6, SR.sup.6, S(O)R.sup.6, S(O).sub.2 R.sup.6, CO.sub.2 R.sup.7, C(O)NR.sup.8 R.sup.9, S(O).sub.2 NR.sup.10 R.sup.11, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 haloalkenyl, NO.sub.2, CN, C(O)R.sup.12, or C.sub.1 -C.sub.2 alkyl substituted by C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or CN; PA1 R.sup.6 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.3 alkenyl, C.sub.2 -C.sub.3 haloalkenyl, propargyl, cycloproyl or cyclopropylmethyl. PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl or OCF.sub.2 H; PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, CH(OCH.sub.3).sub.2 or cyclopropyl; and PA1 R is H.
U.S. No. 4,622,062 disclosed herbicidal sulfonylureas of the formula ##STR3## wherein L, in part, is ##STR4## Q.sub.1 is O, S or SO.sub.2.
U.S. No. 4,643,759 discloses herbicidal compounds of the formula ##STR5## wherein Q is ##STR6## W is O, S or NR.sub.3
U.S. No. 4,678,499 discloses herbicidal compounds of the formula ##STR7## wherein Q is ##STR8## G is CH.sub.2, CH.sub.2 CH.sub.2, O, S, NH, NCH.sub.3 or CH.dbd.CH; G.sub.1 is CH.sub.2, CH.sub.2 CH.sub.2 or CH.dbd.CH;
U.S. No. 4,671,817 discloses herbicidal compounds of the formula ##STR9## wherein L is ##STR10##
U.S. No. 4,723,987 discloses herbicidal compounds of the formula ##STR11## wherein J is ##STR12## E is a bridge of 3 or 4 atoms, which may be substituted or unsubstituted, containing 0-2 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, and also containing 1-4 atoms of carbon, said bridge together with two carbon attachment sites forming a partially saturated 5- or 6-membered carbocyclic or heterocyclic ring; or E is a bridge of 3 or 4 atoms, which may be substituted or unsubstituted, containing 0-1 heteroatoms selected from oxygen or sulfur, 0-2 heteroatoms of nitrogen and 1-4 atoms of carbon said bridge together with two carbon attachment sites forming a fully unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, with the proviso that when E contains two atoms of oxygen or sulfur, they must be separated by at least one atom of carbon, and the oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO.sub.2 ; in the bridging group E, sulfur may take the form of S, SO or SO.sub.2, and one of the atoms of carbon may be a carbonyl, thiocarbonyl or the cyclic 5- and 6-membered ketals thereof.
South African Patent Application 84/8844 and its equivalent U.S. No. 4,605,433, discloses substituted 1,2,4-triazolo-[1,5-a]pyrimidine-sulfonamides of the following formula as herbicides and plant growth regulants. ##STR13##
U.S. No. 4,685,958, discloses substituted 2-amino-1,2,4-triazolo[1,5-A]-1,3,5-triazines of the following formula as herbicides. ##STR14##
EP-A-244,097, published on Nov. 4, 1987, discloses herbicidal pyrazolopyrimidine derivatives of the formula ##STR15## wherein X is --NR--SO.sub.2 --, --SO.sub.2 --O--, --SO.sub.2 --NR-- or --S(O).sub.n CR'R"--.
EP-A-244,098, published on Nov. 4, 1987, discloses herbicidal thiazolotriazolesulfonamides of the formula ##STR16##
U.S. Ser. No. 07/039492 which was allowed discloses herbicidal benzotriazole sulfonylureas.
EP-A-244,166, published Nov. 4, 1987, discloses herbicidal compounds of the formula ##STR17## wherein L, in part, is a benzene, naphthalene, pyrazole, thiophene, pyridine, benzothiophene or an indole moiety;
EP-A-238,070, published Sept. 23, 1987, discloses compounds of the formula ##STR19## wherein Q is a condensed heterocyclic group having N atoms in the bridgehead which may be substituted;